Diastereoselective Synthesis of 1,2-Diamines by Palladium Catalyzed Aza-Claisen Rearrangement

Josef Gonda; Anne-Charlotte Helland; Beat Ernst; Daniel Belluš

doi:10.1055/s-1993-25930

Synthesis 1993; 1993(7): 729-734
DOI: 10.1055/s-1993-25930

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Diastereoselective Synthesis of 1,2-Diamines by Palladium Catalyzed Aza-Claisen Rearrangement

Josef Gonda^* , Anne-Charlotte Helland, Beat Ernst, Daniel Belluš

^*Corporate Research Units, Ciba-Geigy AG, CH-4002 Basel, Switzerland

Abstract

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In the thermal rearrangement of allylic trichloroacetimidates 6, no 1, 2-asymmetric induction can be observed. Palladium(II) catalyzed, however, the rearrangement takes place at 25°C and yields diastereoselectively (de ≥ 98%) the anti-1,2-diamines 7. The allylic trichloroacetimidates 6 can easily be prepared starting from α-amino acids.

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